Managing your success: Boss relationships

Jodie Charlop

by Jodie Charlop 82Ox 85C
Executive Career Coach, EAA
October 2010


Okay. I must admit I’m a fan of The Apprentice. Maybe it’s my fascination with how badly professional people can behave on national television, but I can rationalize watching, since I’m a coach and in the human behavior business.

In week four of this season, Donald Trump fired a young professional named Tyana. Tyana had a strong project win the prior week, so she looked safe. But in the week four episode, it was clear Tyana didn’t like the week’s project leader or agree with the direction of the assignment. Tyana made a strategic error when she took a backseat role and checked out.

If you watch the show, you’ll know The Donald is pretty adamant: if you stay—regardless of your feelings— you better show up and play! But it did bring up a great question. How do you show up for a difficult or challenging boss?

As a career coach, I hear my clients’ greatest frustrations as they navigate and orchestrate their professional success – and one of the most common topics is managing the boss relationship. Research shows that people don’t leave jobs, they leave bad bosses.

How you handle a difficult boss can make or break your career. Yes, it would be marvelous if all bosses developed their people and exhibited wonderful leadership skills, but over time, I find clients who manage up effectively to their bosses are more successful than those who don’t. Please note, I’m not talking about abusive or toxic bosses. I’m addressing bosses who may have different styles, management approaches, or belief systems than you.

Let’s take John, for example. John works in the financial arena in a Fortune 50 company. In coaching, he has worked hard to advance in his career, and has been promoted twice since I met him. He was very happy with his career trajectory, increased responsibility, and the additional compensation and bonus plan that accompanied each milestone.

John took his own management style and leadership very seriously. In his own 360 feedback surveys, he received excellent marks from his boss, peers, and direct reports on his empowering leadership style. However, when his new boss, Sharon, took over his business unit, John came to coaching to discuss if he should stay or go. Sharon had a reputation as a difficult, detail-driven person known for her micromanaging ways and an intense critical side—the opposite of John’s style. Colleagues said he should consider a move, but the skills and experience he was gaining at his organization were well-aligned to his long-term career goals.

John stayed and committed to working with Sharon. In the beginning, John did find Sharon’s style draining, but coaching helped him depersonalize her micromanagement. He reframed issues and learned to manage their relationship productively. John assessed Sharon’s work pressures and observed her work style so he could anticipate her needs and consistently give her what she needed.

After about three months, John felt he was reading her well enough to smooth out most major difficulties. While co-workers talked about the difficulties of working with Sharon, John felt he needed to support her.

I asked John to identify what he admired or liked about Sharon. Although he disagreed with her management styles, John found many things he liked about her—the way she managed executives in meetings, her good insight into business problems, and her ability to utilize data.

John provided authentic, positive feedback to Sharon and her boss on her strengths. Over time, Sharon’s tone lightened with him as he won her trust and respect. So was it really a surprise when Sharon advocated for John to be advanced to the officer track? John had made a strategic decision to positively manage the relationship with Sharon with excellent results. Was it easy? No. But did it have positive impact to John’s career? Yes!

A leader in today’s complex landscape must gain the skills to work effectively with others – even if their style, approach, and knowledge is different from his/her own. To help you assess if you have a strong, powerful relationship with your boss, consider the following checklist. Do you:

1. Create and nurture a strong relationship with your boss?
2. Read your boss well – moods, behaviors, work style – and adapt your approach to his/her style?
3. Take proactive steps to ensure you and your boss are on the same page at least 90 percent of the time?
4. Proactively align your work deadlines and priorities to your boss’s most critical priorities?
5. Get on your boss’s calendar at least once a week to ensure you are in sync?
6. Get on your boss’s calendar at least once a month for big-picture discussion and get feedback to ensure you are meeting his/her needs effectively?
7. Notify your boss of any pending surprises well in advance (i.e., practice a no-surprise rule)?
8. Demonstrate you can problem-solve, yet know when to keep your boss in the loop?
9. Communicate and negotiate with confidence with your boss on tough issues?
10. Back your boss even when he/she goes in a direction you don’t agree with?
11. Routinely give your boss authentic praise directly, and up the hierarchy to his boss, when possible? Bosses need praise, too.
12. Show positive regard and respect to your boss—even when you may not agree with his/her decisions?
13. Demonstrate behaviors that show your boss that you have his/her back—especially with key stakeholders within the organization?
14. Serve as your boss’s extra eyes and ears on issues important to him and your department?
15. Present objectively and manage your emotions well in the workplace?
16. Proactively work to earn your boss’s respect by showing up as a leader and managing your business well in the workplace?

Boss relationships can make or break your career—help or hinder your next promotion—and set the tone for your leadership. Take a moment to reflect on your relationship with your current boss. On a scale of 1 to 10, how would you rate the effectiveness of your relationship? If it’s anything less than a 10 and you want to advance in your career, you might have identified an area for your professional development.


The EAA’s Executive Career Coach Jodie Charlop 82Ox 85C, founder and chief coaching officer for Potential Matters, specializes in working with individuals and organizations that want to achieve higher levels of personal and professional results in their business, careers, or lives.